3-R-methyl-7-amino-ceph-em-4-carboxylic acid compounds

Abstract

3-R-Methyl-7-amino-ceph-2-em-4ξ-carboxylic acid compounds, in which R is the C-residue of a C-nucleophilic compound are valuable intermediates, for example, in the manufacture of the corresponding 3-R-methyl-7-amino-ceph-3-em-4-carboxylic acid compounds with antibiotic properties.

We claim: 
     
       1. Compounds having the formula ##SPC8## in which R" represents 2- or 4-hydroxy-phenyl, 2,5- or 3,4-dihydroxy-phenyl, 2- or 4-lower alkoxy-phenyl, 2,4-, 2,5- or 3,4-dimethoxy-phenyl, 2- or 4-lower alkanoyloxy-phenyl, 4-lower alkylthio-phenyl, 2-thienyl, 2-furyl, 5-carboxy-2-furyl or 5-lower alkoxycarbonyl-2-furyl, and in which R.sub. 1 ' represents an acyl radical of the formula ##EQU3## in which Ar represents phenyl, 3- or 4-hydroxy-phenyl, 3-chloro-4-hydroxy-phenyl, 3,5-dichloro-4-hydroxy-phenyl or thienyl, and R 3   represents hydrogen, amino, t-lower alkoxycarbonylamino, 2-halogenolower alkoxycarbonylamino, guanylureido, sulphoamino, carboxyl or sulpho, and R.sub. 2 ' represents hydrogen or tert.-lower alkyl, 2-halogenlower alkyl, phenacyl, benzhydryl, 4,4'-dimethoxy-diphenylmethyl or lower alkanoyloxymethyl, and pharmaceutically acceptable salts of such compounds having salt-forming groups.   
     
     
       2. A compound as claimed in claim 1 and being a member selected from the group consisting of 7β-phenylacetylamino-3-(2-thenyl)-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof. 
     
     
       3. A compound as claimed in claim 1 and being a member selected from the group consisting of 3-(5-methoxycarbonyl-furfuryl)-7β-phenylacetylamino-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof. 
     
     
       4. A compound as claimed in claim 1 and being a member selected from the group consisting of 3-(4-hydroxybenzyl)-7β-phenylacetyl-amino-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof. 
     
     
       5. A compound as claimed in claim 1 and being a member selected from the group consisting of 3-(4-acetyloxybenzyl)-7β-phenylacetyl-amino-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof. 
     
     
       6. A compound as claimed in claim 1 and being a member selected from the group consisting of 3-(2-thenyl)-7β-[D-(α)-phenylglycyl]-amino-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof. 
     
     
       7. A compound as claimed in claim 1 and being a member selected from the group consisting of 7β-amino-3-(5-methoxycarbonyl-furfuryl)-ceph-3-em-4-carboxylic acid, or pharmaceutically acceptable salts thereof. 
     
     
       8. A compound as claimed in claim 1 and being a member selected from the group consisting of 3-(4-hydroxybenzyl)-7β-[D-(α)-phenylglycyl]-amino-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof. 
     
     
       9. A compound as claimed in claim 1 and being a member selected from the group consisting of 3-(4-acetyloxybenzyl)-7β-[D-(α)-phenylglycyl]-amino-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof. 
     
     
       10. A compound as claimed in claim 1 and being a member selected from the group consisting of 3-(5-methoxycarbonyl-2-furfuryl)-7β-[ D-(α)-phenylglycyl]-amino-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof.